IMPPAT Phytochemical information: 
Geniculatin
Geniculatin
Summary

SMILES: COc1c(O)cc2c(c1O)c(=O)c(c(o2)c1ccc(cc1)O)O[C@@H]1O[C@H](COC(=O)C2C(c3ccc(cc3)O)C(C2c2ccc(cc2)O)C(=O)OC[C@H]2O[C@@H](Oc3c(oc4c(c3=O)c(O)c(c(c4)O)OC)c3ccc(cc3)O)[C@@H]([C@H]([C@@H]2O)O)O)[C@H]([C@@H]([C@H]1O)O)O
InChI: InChI=1S/C62H56O28/c1-81-55-31(67)19-33-39(45(55)71)47(73)57(53(85-33)25-7-15-29(65)16-8-25)89-61-51(77)49(75)43(69)35(87-61)21-83-59(79)41-37(23-3-11-27(63)12-4-23)42(38(41)24-5-13-28(64)14-6-24)60(80)84-22-36-44(70)50(76)52(78)62(88-36)90-58-48(74)40-34(20-32(68)56(82-2)46(40)72)86-54(58)26-9-17-30(66)18-10-26/h3-20,35-38,41-44,49-52,61-72,75-78H,21-22H2,1-2H3/t35-,36-,37?,38?,41?,42?,43-,44-,49+,50+,51-,52-,61+,62+/m1/s1
InChIKey: NNBOPQPMWAVYCT-FRVZIGEWSA-N
DeepSMILES: COccO)cccc6O))c=O)cco6)cccccc6))O))))))O[C@@H]O[C@H]COC=O)CCcccccc6))O)))))CC4cccccc6))O))))))C=O)OC[C@H]O[C@@H]Occoccc6=O))cO)ccc6)O))OC)))))))cccccc6))O))))))))[C@@H][C@H][C@@H]6O))O))O))))))))))))))[C@H][C@@H][C@H]6O))O))O
Scaffold Graph/Node/Bond level: O=C(OCC1CCCC(Oc2c(-c3ccccc3)oc3ccccc3c2=O)O1)C1C(c2ccccc2)C(C(=O)OCC2CCCC(Oc3c(-c4ccccc4)oc4ccccc4c3=O)O2)C1c1ccccc1
Scaffold Graph/Node level: OC(OCC1CCCC(OC2C(O)C3CCCCC3OC2C2CCCCC2)O1)C1C(C2CCCCC2)C(C(O)OCC2CCCC(OC3C(O)C4CCCCC4OC3C3CCCCC3)O2)C1C1CCCCC1
Scaffold Graph level: CC(CCC1CCCC(CC2C(C)C3CCCCC3CC2C2CCCCC2)C1)C1C(C2CCCCC2)C(C(C)CCC2CCCC(CC3C(C)C4CCCCC4CC3C3CCCCC3)C2)C1C1CCCCC1
Functional groups: CO; COC(C)=O; c=O; cO; cOC; cO[C@@H](C)OC; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Flavonoids
ClassyFire Subclass: Flavonoid glycosides
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Flavonols
Synonymous chemical names:
geniculatin
External chemical identifiers:
CID:57408283
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Geniculatin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 1249.1
Log P RDKit 2.87
Topological polar surface area (Å2) RDKit 451.62
Number of hydrogen bond acceptors RDKit 28
Number of hydrogen bond donors RDKit 14
Number of carbon atoms RDKit 62
Number of heavy atoms RDKit 90
Number of heteroatoms RDKit 28
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 10
Stereochemical complexity RDKit 0.16
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 44
Number of sp3 hybridized carbon atoms RDKit 18
Shape complexity RDKit 0.29
Number of rotatable bonds RDKit 18
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 6
Number of aromatic heterocycles RDKit 2
Number of aromatic rings RDKit 8
Total number of rings RDKit 11
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 11
Geniculatin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 3
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.0618